Perylene-based materials for organic photoelectric conversion layers

Patent metadata

Field	Value
Publication number	US-9978951-B2
Application number	US-201515128194-A
Country	US
Kind code	B2
Filing date	Mar 20, 2015
Priority date	Mar 31, 2014
Publication date	May 22, 2018
Grant date	May 22, 2018

Abstract

The present disclosure relates to perylene-based molecules and their use in photoelectric conversion layer(s) and/or an organic or hybrid image sensor. The present disclosure also relates to absorption layer(s) and photoelectric conversion layer(s) comprising a molecule according to the present disclosure. The present disclosure also relates to a device, comprising a photoelectric conversion layer comprising at least one perylene-based molecule. Moreover, the present disclosure relates to an organic image sensor or a hybrid Silicon-organic image sensor comprising photoelectric conversion layer(s) according to the present disclosure.

First claim

The invention claimed is:

1. A molecule represented by a general formula selected from I, II or III:

wherein
X, and Y are the same or different and are, at each occurrence, independently selected from the following electron donating groups (EGD) and electron withdrawing groups (EWD):

or hydrogen, wherein in formula III, when Y is hydrogen and each X is the same,
wherein R is independently selected from hydrogen, an alkyl or aryl substituent,
Z, at each occurrence, is independently selected from the following electron donating groups (EGD) and electron accepting groups (EAD):

hydrogen or —OCH 3 , wherein in formula III, when X and Y are H, Z is not —OCH 3 , hydrogen or

W, at each occurrence, is independently selected from the following electron donating groups (EGD) and electron withdrawing groups (EWD):

 wherein
R is independently selected from hydrogen, an alkyl or aryl substituent,
n is an integer selected from 1 to 10, and
Ri, at each occurrence, is independently selected from:

wherein, W, X, and Y are not cyano, nitro, quaternary amino, sulfo, carbonyl, substituted carbonyl, or carboxy.

2. The molecule according to claim 1 ,
wherein the molecule is represented by formula I, and X, Y and Z are H, and W is as defined in formula I.

3. The molecule according to claim 1 , wherein the molecule is represented by formula II and Ri is as defined formula II, X, Y and Z are H, and W is an electron donating group (EDG) as defined in formula II,
wherein the molecule is represented by any of the following structures:

4. The molecule according to claim 1 , wherein the molecule is represented by formula III and
Ri is as defined in formula III,
X is electron donating groups (EDG) as defined in formula III,
Y is H and
Z is H,
wherein the molecule is represented by any of the following structures:

5. The molecule according to claim 1 , wherein the molecule is represented by formula III and
Ri is as defined in formula III,
X is electron withdrawing group (EWG) as defined in formula III,
Y is H, and
Z is H,
wherein the molecule is represented by any of the following structures

6. The molecule according to claim 1 , wherein the molecule is represented by formula III and
Ri is as defined in formula III,
X and Y are H, and
Z is an electron withdrawing or electron donating group (EWG and EDG) as defined in formula III,
wherein the molecule is represented by any of the following structures:

7. The molecule according to claim 1 represented by any of the following structures:

wherein
R is independently selected from hydrogen, an alkyl or aryl substituent, and
n is an integer selected from 1 to 10.

8. The molecule according to claim 1 , wherein the molecule exhibits:
absorption in the visible wavelength range about 400 to about 700 nm,
an extinction coefficient of >10 4 Lmol −1 cm −1 , and/or
high thermal stability, up to at least about 300° C. or up to at least about 300 to 500° C.

9. The molecule according to claim 8 , wherein the molecule
exhibits absorption in the wavelength range of visible light, in the range from 400 nm to 700 nm, or a sub-range thereof, 400 nm to 500 nm, or 500 nm to 600 nm, or 600 nm to 700 nm,
absorbs in the blue absorption range or absorbs in the green absorption range or absorbs in the red absorption range, and/or
absorbs less than 20% of the maximum absorption outside of its main range of absorption.

10. An absorption layer and/or a photoelectric conversion layer and/or in an organic and/or hybrid module for optoelectronic application, comprising organic photoelectric conversion layer(s), OLED and OTFT organic modules comprising the molecule according to claim 1 .

11. A photoelectric conversion layer comprising a molecule according to claim 1 .

12. An absorption layer comprising a molecule according to claim 1 .

13. A device comprising a photoelectric conversion layer comprising the molecule according to claim 1 ,
wherein said device is an organic image sensor, an hybrid image sensor, photodiode, organic photovoltaics, organic light-emitting diode (OLED), or an organic thin-film transistor (OTFT).

14. The device according to claim 13 , wherein said photoelectric conversion layer exhibits photo response in the visible absorption range.

15. The device according claim 13 , further comprising molecule(s) according to general formula I, II or III or photoelectric conversion layer(s) comprising a molecule according to general formula I, II or III.

16. An organic image sensor, comprising
(a) an organic photoelectric conversion unit comprising photoelectric conversion layer(s) comprising the molecule according to claim 1 ,
(b) at least one electrode,
(c) a substrate,
(d) a second electrode on top of said photoelectric conversion layer(s).

17. A hybrid silicon-organic image sensor or organic image sensor, comprising
(a) an organic photoelectric conversion unit or units comprising photoelectric conversion layer(s) comprising the molecule according to claim 1 ,
(b) a Si based photoelectric conversion unit,
(c) metal wiring,
(d) a (CMOS) substrate, and
(e) insulating layer(s).

18. The organic image sensor according to claim 16 , wherein said organic photoelectric conversion unit comprises another layer, which may be an n-type material, p-type material, n-buffer layer and/or p-buffer layer or combinations or mixtures thereof.

19. The molecule according to claim 1 , wherein, in formula III, Ri is not the following group:

Assignees

• Sony Corp

Inventors

• Rosselli Silvia
• Miteva Tzenka
• Nelles Gabriele
• Bamedi Zilai Ameneh
• Deichmann Vitor

Classifications

• C09K11/06 Primary

  containing organic luminescent materials · CPC title

• H01L51/0062 Primary

  Electricity · mapped topic

• C07D209/86 Primary

  with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system · CPC title

• C07D409/04

  directly linked by a ring-member-to-ring-member bond · CPC title

• C07D401/04

  directly linked by a ring-member-to-ring-member bond · CPC title